Quicken (kinda like quickbooks lite. ) is overkill for 13 properties in 2 states plus personal funds.

But for now, is it overkill to set up payments with a servicer like FCI, Madison Management, Polaris, FCI, PPR, Allied Servicing, or ZimpleMoney for this one-off deal?

For now, try to understand the real source of his apathy because showing him the door might be an overkill. 

But vacancy and turn over KILL landlords.if you have gone 2 months without a tenant  and rent is lets say for easy math 1500 a month you lost 3k and your trying for 1750 or whatever its not renting end of the day you will end up lowering the rent to 1500.. and you lost 3500 you will NEVER recover and so how does that make your numbers work.. very often it makes it negative cash flow for that year and or a little longer. 

Is it worth my time and money to get the full GC licensing or is that overkill? 

What would be considered overkill for a C class flip?

@Kevin LefeuvreAn LLC for each property is generally considered an overkill, unless they are large commercial properties or apartments.

Rates seem a little high but don't really know the scope and how detailed the project is, could be in line or way over kill.

Obviously that’s something that a good real estate agent should absolutely know about and it seems like you have had some difficulties getting that information from your current agent.There are several good agents who monitor Bigger Pockets regularly; I’m sure that some of them will chime in here, but if they don’t, let me know and I can certainly connect you with some good ones.Depending on your time or how much you are in Rhode Island, you could also try to go to a local real estate meet up such as RIREIG to connect with other investors to talk about areas.But if you’re just looking for a single property and you’re based out of New York, that might be kind of overkill, and you might just need to find a more experienced real estate agent (at least based on what you posted).

For some its over kill but we send out a text messages and emails on the 30th of the month alerting the client that rent is due.